Tuscany & Florence with Angie Rito and Scott Tacinelli

Day 1: Florence

Benvenuti in Italia! Our adventure through the world’s premier wine destination begins in Florence, the Tuscan capital brimming with art, culture, and positively exquisite cuisine.

We’ll ease into our first day with an unhurried afternoon at the hotel, luxuriating in the opportunity to refresh and get settled after our long transatlantic flights. When the evening rolls around, we’ll reconvene at the Baglioni hotel—not only is it the perfect backdrop to take in all of Florence, but it’s also the site of Angie and Scott’s wedding reception.

Here, we’ll pay homage to their partnership and to one of Italy’s long-standing traditions: the aperitivo. Over welcome drinks and plenty of bright, local fare, we’ll learn more about Angie and Scott’s connection to Florence and Tuscany.

Day 2: Florence

After a slow morning, we’ll head over to Mercato Centrale, one of Europe’s oldest and busiest covered markets, where Angie and Scott will help us navigate the bustle of this thriving marketplace. We’ll taste as we go, sampling local delicacies before sitting down for a traditional Tuscan lunch at one of the market’s most storied stands.

Next, we’ll meander through the historic Santo Spirito district, paying special attention to the city’s 150-odd buchette del vino: small windows attached to the palaces of grand noblemen from which wine was traditionally sold by the fiasco (bottle).

Our final stop is the Accademia, one of Europe’s oldest drawing schools and home to the world’s largest collection of sculptures by Michelangelo. There’s so much to experience here, and with the help of our expert guide we’ll skip the lines and enjoy a beautifully curated tour.

Dinner tonight is at Trattoria Camillo—a casual white tablecloth restaurant that serves classic Tuscan comfort food and just so happens to be a favorite of Scott and Angie’s.

Day 3: Lucca & Pisa

After breakfast, we’ll head out for a day of exploration. Our first stop will be the perfectly preserved town of Lucca, whose medieval walls encircling the centro storico form a vast green space perfect for cycling.

After touring the city on bicycle, we’ll enjoy lunch at a typical Lucchese trattoria, where we’ll sample local dishes like tordelli, a hearty pasta stuffed with Swiss chard and pine nuts. As we dine, our hosts will tell us all about the origins of cucina povera and how both poverty and innovation have shaped this region’s storied cuisine.

We’ll continue onwards to Pisa, a city that—its leaning famous tower notwithstanding—is always reinventing itself and constantly pulsing with vibrancy and life. After a tour of this fabled city, we’ll transfer back to Florence for an evening of independent exploration. Need a dinner recommendation? Scott and Angie have a few favorite places just a stone’s throw away.

Day 4: Panzano

If the weather cooperates, we’re starting the day off in elevated luxury—literally. As the sun rises over the countryside, we are floating high above Tuscany’s patchwork quilt of rolling vineyards, medieval towns, and ancient forests in vibrant hot air balloons.

Once we return to the ground, our first stop is the extraordinary Officina della Bistecca. Dario Cecchini is an international legend, Netflix star and the beating heart behind this cozy neighborhood restaurant and ethical butcher shop — he’s renowned throughout Italy for his commitment to honoring the animal and using all of its parts. Over a spread of seared carpaccio, Florentine steaks, and innovative vegetarian entrees, we’ll toast to the unparalleled splendor of a day well spent in Tuscany.

And just when the day is bordering upon pure bliss, we’ll elevate things to new heights with a stop at a wine estate, famous for its Chianti. Here, we’ll meet the winemakers who are close friends with Angie and Scott.

As the sun stumbles down the horizon, we’ll wend our way back home to our idyllic Tuscan retreat for a casual dinner in our hotel’s restaurant.

Day 5: Siena

As the sun makes its giddy debut over bright-eyed Florence, seize the day with an optional yoga session. After a sumptuous breakfast, we’ll make our way to gracious Siena. It’s arguably one of the most beautiful cities in all of Italy, with a car-free central district of ancient alleyways and noble squares. We’ll walk the same cobbled lanes that locals walked in the middle ages, while learning about the rich history of this ancient city.

After this initial immersion, we’ll dive deeper into the unique history of Siena with a visit to a local test kitchen for an apron-clad, sleeves-rolled, flour-dusted and only-in-Tuscany pasta workshop. Alongside Scott and Angie, we’ll learn the intricacies of shaping, setting and boiling pasta; the experience we’ll end with a few hearty cheers and our whole group seated and sampling our very own creation.

After some relaxation time at the hotel, we’ll reconvene for a local dinner, where the menu hasn’t changed in decades and their wine cellar is home to some truly remarkable vintages.

Day 6: Marina di Grossetto

This morning, we’ll head to Marina di Grossetto for a day of aquatic adventure. With white sand beaches that stretch for miles, the region is a stunning exemplar of Tuscany’s natural beauty—which, of course, we’ll be exploring in style. From breezy sailboats, we’ll bask in the magnificence of our surroundings, cooling off with a swim or snorkel (if it’s warm enough) before a hyperfresh lunch onboard.

For dinner, we’re taking advantage of our coastal location and indulging in a Tuscan seafood feast. As we breathe in the salty sea air at a nearby restaurant (a favorite among locals), we’ll share our favorite memories from the day and savor the impeccable flavor of just-caught frutti di mare.

Day 7: Tuscany

This morning is all about the gifts of the countryside. After a visit to the medieval village of Pienza, we’ll wander down the road a spell to one of the area’s dairy farms, where we’ll sample some of the best cheeses in Tuscany. What follows is a equally enchanting affair, a vineyard picnic dominated by local wine and a symphony of fresh, seasonal offerings.

In the afternoon, we’re heading back to reflect on the magic of our morning. Drink in the warm afternoon sun from the terraced garden, or hit the reset button with a nourishing massage at the in-house spa. We won’t meet up again until later in the evening for dinner, and trust us on this one—it’s a truly remarkable experience. While we don’t want to give any spoilers, we’ll leave it as this: we’re in for an intimate evening of celebration, heartfelt flavors, and friends we’ll cherish for the years to come.

Day 8: Departures

Arrivederci Italia! After eight full days of immersion in the best Italy has to offer, it’s time to say ciao to Scott and Angie and to each other, knowing the memories we’ve made will stay with us for a lifetime. Until we meet again!